Acetic Anhydride → 1-(3-Benzyloxy-6-methoxyphenyl)-1-(5-methoxy-2-pyridyl)-methyl acetate

HRID 35293ノート

反応式

HRID 35293 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][N:3]=1.C([Li])CCC.[CH2:15]([O:22][C:23]1[CH:24]=[CH:25][C:26]([O:31][CH3:32])=[C:27]([CH:30]=1)[CH:28]=[O:29])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:33](OC(=O)C)(=[O:35])[CH3:34]>N1C=CC=CC=1.CO>[C:33]([O:29][CH:28]([C:27]1[C:26]([O:31][CH3:32])=[CH:25][CH:24]=[C:23]([O:22][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:30]=1)[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][N:3]=1)(=[O:35])[CH3:34]

参加物

7

反応物 4

HCID 7918Acetic AnhydrideHCID 109666945-(Benzyloxy)-2-methoxybenzaldehydeHCID 111481512-Bromo-5-methoxypyridineHCID 178418339Butyllithium

生成物 1

HCID 143331241-(3-Benzyloxy-6-methoxyphenyl)-1-(5-methoxy-2-pyridyl)-methyl acetate収率 50%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 1049Pyridine溶媒

実験手順

2-Bromo-5-methoxypyridine (15.35 g) was successively treated with n-butyl lithium and 5-benzyloxy-2-methoxybenzaldehyde (16.47 g, Example 1(i)) under the conditions of Example 1(j). The crude carbinol (19.4 g) was treated with acetic anhydride and pyridine as described in Example 1(k). The product was purified by column chromatography on silica gel (550 g). Elution with petroleum spirit (60°-80°)/ethyl acetate (2:1), then recrystallisation from dichloromethane/petroleum spirit gave 1-(3-benzyloxy-6-methoxyphenyl)-1-(5-methoxy-2-pyridyl)-methyl acetate (13.29 g, 50%), m.p. 105°-110°.

後処理

  1. customThe product was purified by column chromatography on silica gel (550 g)
  2. washElution with petroleum spirit (60°-80°)/ethyl acetate (2:1)
  3. customrecrystallisation from dichloromethane/petroleum spirit

出典と根拠

ORDレコード
ord-b7bab98b81dd41709368811db9a74746
出典データセット
uspto-grants-1988_08
特許番号
US04766121

反応ノート

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